That's a pretty large spread of geography and look/feel.
What kind of place are you looking for? What kind of feel? Big town, metropolitan, small-town, etc? Hard to answer without knowing your tolerance to congestion, whether you can deal with "small town" limitations, big-city-style impersonal treatment, etc.


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Now, that I said that, I hope you don't live there Carl. All these places are nice and tend to be on the more expensive side. There are some good deals to be made now with the economy changes and short sales available. Winter Park always has over-inflated home prices and ridiculous taxes. For $99K you'd be lucky to find a decent condo. Here are a couple of the better known realtor's in Winter Park so you can get some ideas: (from $8 million and down)
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